Frank Sinatra (1915-1998) was an iconic American singer, actor, and producer who is widely regarded as one of the greatest entertainers of the 20th century. Born in Hoboken, New Jersey, Sinatra began his musical career in the swing era as a vocalist with Harry James and Tommy Dorsey’s orchestras in the early 1940s. He quickly rose to fame as a solo artist, becoming known for his smooth voice, impeccable phrasing, and emotional delivery.
Sinatra’s career spanned over six decades, during which he achieved numerous chart-topping hits, won multiple Grammy Awards, and starred in many acclaimed films. Some of his most famous songs include “My Way,” “Fly Me to the Moon,” “New York, New York,” “Strangers in the Night,” and “Come Fly with Me.”
In addition to his music career, Sinatra was a successful actor, appearing in over 60 films. He won an Academy Award for Best Supporting Actor for his role in “From Here to Eternity” (1953) and received critical acclaim for his performances in movies such as “The Manchurian Candidate” (1962) and “The Man with the Golden Arm” (1955).
Sinatra’s influence on popular culture is immense, and he remains an enduring icon in the worlds of music and film. Often referred to as “Ol’ Blue Eyes” or simply “The Chairman of the Board,” Sinatra’s legacy continues to resonate with audiences around the world.
1. My Way
“My Way” is a song closely associated with Frank Sinatra, although it was originally written by Paul Anka and released by him in 1969. Sinatra’s rendition, however, became the definitive version and one of his signature songs. He recorded it in 1968 and released it on his album of the same name, “My Way,” in 1969.
The song’s lyrics reflect on a life lived with individuality and self-determination, expressing defiance and pride in one’s choices and the ability to face life’s challenges on one’s own terms. The refrain, “I did it my way,” encapsulates the theme of independence and self-assurance.
“My Way” became one of Sinatra’s most enduring hits, and it remains one of the most popular and recognizable songs in his repertoire. It has been covered by numerous artists and has been used in various forms of media, solidifying its status as a classic in the American songbook and an anthem of self-empowerment.
2. Fly Me to the Moon
“Fly Me to the Moon” is a popular jazz standard written by Bart Howard in 1954. It has been performed by many artists over the years, but it was made famous by Frank Sinatra, whose rendition became particularly well-known.
The song’s lyrics describe a longing to be taken away on a romantic journey to space, where the moon serves as a metaphorical destination. The imagery evokes feelings of wonder, adventure, and romance.
Sinatra’s version of “Fly Me to the Moon” was included on his 1964 album “It Might as Well Be Swing,” which was arranged and conducted by Quincy Jones. Sinatra’s smooth vocals combined with the lush orchestration created a timeless and enchanting rendition of the song.
“Fly Me to the Moon” has since become a jazz standard, covered by countless artists in various styles and genres. It continues to be a beloved and frequently performed song, cherished for its beautiful melody and evocative lyrics.
3. I’ve Got You Under My Skin
“I’ve Got You Under My Skin” is a classic song written by Cole Porter in 1936. It has been performed by numerous artists over the years, but it is most famously associated with Frank Sinatra.
The song’s lyrics describe the experience of being deeply in love and unable to shake the feeling of longing for someone, almost as if they are under one’s skin. The metaphorical imagery evokes the intensity of romantic desire and the inability to escape its hold.
Sinatra’s rendition of “I’ve Got You Under My Skin” was released in 1956 as part of his album “Songs for Swingin’ Lovers!” His smooth and emotive vocals, combined with Nelson Riddle’s orchestration, helped propel the song to become one of Sinatra’s signature tunes.
Over the years, “I’ve Got You Under My Skin” has become a jazz standard, covered by numerous artists in various styles. It remains a timeless and enduring classic, cherished for its beautiful melody, sophisticated lyrics, and evocative portrayal of love and desire.
4. Strangers in the Night
“Strangers in the Night” is a popular song written by Bert Kaempfert, Charles Singleton, and Eddie Snyder in 1966. It was originally composed as an instrumental titled “Beddy Bye” for the movie “A Man Could Get Killed.” However, after Frank Sinatra heard it, he requested lyrics be added, resulting in the version we know today.
Frank Sinatra’s recording of “Strangers in the Night” became a huge hit, topping the charts in both the United States and the United Kingdom. Released in 1966 as a single and later included on his album of the same name, the song is characterized by its romantic lyrics and catchy melody.
The song tells the story of two strangers who meet one night and share a fleeting romantic encounter. It evokes the excitement and uncertainty of newfound love, with the refrain “Strangers in the night, exchanging glances, wondering in the night, what were the chances?” becoming iconic.
“Strangers in the Night” won the Grammy Award for Record of the Year in 1967 and remains one of Sinatra’s most recognizable and beloved songs. Its lush orchestration and Sinatra’s smooth vocals have made it a timeless classic, often associated with romance and nostalgia.
5. The Way You Look Tonight
“The Way You Look Tonight” is a classic song written by Jerome Kern, with lyrics by Dorothy Fields. It was originally featured in the film “Swing Time” (1936), where it was performed by Fred Astaire. The song won the Academy Award for Best Original Song that year.
“The Way You Look Tonight” is a romantic ballad that expresses admiration and affection for the person being addressed. The lyrics describe the beauty and charm of the individual, capturing the feeling of being captivated by someone’s presence.
Over the years, “The Way You Look Tonight” has become a jazz standard and has been recorded by numerous artists from various genres. Frank Sinatra’s rendition of the song is particularly famous and remains one of the most beloved interpretations. It has been featured in countless films, TV shows, and commercials, and it continues to be performed by singers around the world, making it a timeless classic in the American songbook.
6. That’s Life
“That’s Life” is a song originally written by Dean Kay and Kelly Gordon. It was first recorded by Marion Montgomery in 1963. However, the most famous version of the song was recorded by Frank Sinatra in 1966.
Sinatra’s rendition of “That’s Life” was released as a single and also appeared on his album of the same name. The song’s lyrics reflect on the ups and downs of life, acknowledging the setbacks and challenges one may face, but ultimately embracing resilience and perseverance. The refrain, “That’s life, that’s what all the people say. You’re riding high in April, shot down in May,” encapsulates the song’s message of accepting life’s unpredictability and continuing to move forward.
Frank Sinatra’s recording of “That’s Life” became a major hit, reaching the top five on the Billboard Hot 100 chart in the United States. It remains one of Sinatra’s most iconic songs, celebrated for its powerful vocal performance and timeless message. “That’s Life” has been covered by numerous artists over the years and continues to resonate with listeners as a classic anthem of resilience and determination.
7. Come Fly with Me
“Come Fly with Me” is a classic song performed by Frank Sinatra, with music by Jimmy Van Heusen and lyrics by Sammy Cahn. It was written in 1957 for Sinatra’s album of the same name, “Come Fly with Me.” The album was arranged and conducted by Billy May.
The song is an up-tempo jazz standard that invites the listener on a romantic adventure. It conjures images of travel and exploration, with lyrics that evoke the excitement of embarking on a journey with a loved one. Sinatra’s smooth vocals and the swinging arrangement contribute to the song’s infectious energy and sense of wanderlust.
“Come Fly with Me” became one of Sinatra’s signature songs and remains one of his most popular recordings. It has been covered by numerous artists over the years and has been featured in various films, TV shows, and commercials. The song’s enduring appeal has cemented its status as a classic in the Great American Songbook.
8. One for My Baby (And One More for the Road)
“One for My Baby (And One More for the Road)” is a classic song written by Harold Arlen (music) and Johnny Mercer (lyrics). It was first introduced in the 1943 musical film “The Sky’s the Limit,” where it was performed by Fred Astaire. However, it was Frank Sinatra’s rendition of the song that became the most famous.
Sinatra’s recording of “One for My Baby” was released in 1958 as part of his album “Frank Sinatra Sings for Only the Lonely.” The song is a torch ballad that tells the story of a man drowning his sorrows in a bar late at night. He shares his troubles with the bartender while ordering “one for my baby” (a final drink) and “one more for the road” (one more to drink before leaving).
Sinatra’s emotive and nuanced performance, combined with the song’s melancholic melody and Mercer’s poignant lyrics, make “One for My Baby” a timeless classic. The song has since been covered by numerous artists and is considered one of Sinatra’s signature songs. It evokes feelings of loneliness, heartache, and introspection, and it remains a poignant and powerful reminder of the human experience.
9. Witchcraft
“Witchcraft” is a classic song famously performed by Frank Sinatra. It was written by Cy Coleman and Carolyn Leigh and was first recorded by Sinatra in 1957 for his album “Come Fly with Me.”
The song’s lyrics describe the intoxicating effect of falling in love and liken the experience to being under a spell or enchantment, hence the title “Witchcraft.” It evokes a sense of mystery and allure, with references to magical elements such as spells, charms, and bewitching eyes.
Sinatra’s smooth and seductive delivery, combined with the lush orchestration, enhances the song’s romantic atmosphere. “Witchcraft” quickly became one of Sinatra’s signature songs and remains a beloved classic in his repertoire.
Over the years, “Witchcraft” has been covered by numerous artists from various genres, and it has been featured in films, TV shows, and commercials, solidifying its status as a timeless standard in the Great American Songbook.
10. Summer Wind
“Summer Wind” is a classic song written by Johnny Mercer and Henry Mayer in 1965. The song was originally recorded by Wayne Newton, but it became most famous through Frank Sinatra’s rendition.
Sinatra’s recording of “Summer Wind” was released on his 1966 album “Strangers in the Night.” The song describes the fleeting nature of a summer romance, with lyrics that evoke imagery of warm summer nights, gentle breezes, and love that comes and goes like the wind.
Sinatra’s smooth vocals and Nelson Riddle’s lush orchestration contribute to the song’s nostalgic and romantic atmosphere. “Summer Wind” became one of Sinatra’s signature songs and remains a beloved classic in the Great American Songbook.
Over the years, “Summer Wind” has been covered by numerous artists and featured in various films, television shows, and commercials. Its timeless melody and evocative lyrics continue to resonate with listeners, making it a cherished standard in the world of popular music.